(3,4-Dimethoxyphenyl)acetic acid → HCID 12570798, compound

HRID 443735Notes

Reaction equation

HRID 443735 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[NH2:33][C:34]([CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=1)[OH:38])([CH3:36])[CH3:35]>O1CCCC1>[OH:38][CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[CH:40]=1)[C:34]([NH:33][C:12](=[O:14])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 12570782HCID 12570782, compound

Product 1

HCID 12570798HCID 12570798, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 50 g. (0.26 mole) of 3,4-dimethoxyphenylacetic acid, 68 g. (0.28 mole) of EEDQ and 50 g. (0.26 mole) of α-(1-amino-1-methylethyl)-3-methoxybenzenemethanol in 450 ml. tetrahydrofuran are stirred for three days at 25° C., and then heated for 5 hours at 65° C. Tetrahydrofuran is evaporated in vacuo, and the residue is taken up with ice and 10% aqueous H2SO4 solution to pH 2. The amide is extracted twice with 500 ml. ethyl acetate. The combined organic extracts are washed with 500 ml. dilute aqueous NH4OH solution, dried (Na2SO4) and evaporated to dryness in vacuo. The residual oil is dissolved in hot diethyl ether from which it crystallizes to give 72.0 g. of impure product. Recrystallization from diethyl ether gives 70 g. (72% yield) of N-(β-hydroxy-3-methoxy-α,α-dimethylphenethyl)-3,4-dimethoxybenzeneacetamide as white crystals of analytical purity, m.p. 137°-138° C.

Workup

  1. customTetrahydrofuran is evaporated in vacuo
  2. extractionThe amide is extracted twice with 500 ml
  3. washThe combined organic extracts are washed with 500 ml
  4. dry with materialdilute aqueous NH4OH solution, dried (Na2SO4)
  5. customevaporated to dryness in vacuo
  6. dissolutionThe residual oil is dissolved in hot diethyl ether from which it
  7. customcrystallizes
  8. customto give 72.0 g
  9. customRecrystallization from diethyl ether
  10. customgives 70 g

Sources & evidence

ORD record
ord-2539738979ac40b594c18c073765a0bf
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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